Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 37 - 48 of 77 rentals matching your search criteria
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Under The Palms

Type

  • Home
2 Bedrooms
2 Baths
4 Guests
Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.

Perfect Pineapple

Type

  • Home
2 Bedrooms
1 Bath
4 Guests
Sit along side your private pool for morning coffee or your evening glass of wine.

Flagler Station

Type

  • Home
3 Bedrooms
2 Baths
6 Guests
With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying.

Casa Grande

Type

  • Home
5 Bedrooms
5.5 Baths
12 Guests
Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions!

Spa Oasis

Type

  • Home
3 Bedrooms
2 Baths
6 Guests
Welcome to a golfer’s paradise at Spa Oasis!

Conch Republic Retreat

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890.

William's Loft

Type

  • Cottage
2 Bedrooms
1 Bath
3 Guests
This perfect spot offers plenty of private outdoor space within walking distance of great restaurants and shops.

Buena Vista

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
The historic brick foundry residence is in the luxurious gated community of the Truman Annex, appropriately named after President Harry Truman.

Beach House Condo

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.

A Place In Paradise

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

City Cay

Type

  • Condo
1 Bedroom
1 Bath
2 Guests
Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This understated Truman Annex Condo is the place!

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